Immunostimulatory activities of monoglycosylated alpha-D-pyranosylceramides.
We compared the immunostimulatory effects of chemically synthesized alpha-galactosylceramides (alpha-GalCers), alpha-glucosylceramides (alpha-GluCers), 6"-monoglycosylated alpha-GalCer and 6"- or 4"-monoglycosylated alpha-GluCer and made the following observations: (1) the length of the fatty acid side chain in the ceramide portions greatly affects the immunostimulatory effects of alpha-GalCers and alpha-GluCers; (2) the configuration of the 4"-hydroxyl group of the inner pyranose moiety plays an important role in the immunostimulatory effects of monoglycosylated alpha-D-pyranosylceramides; (3) the free 4"-hydroxyl group of the inner pyranose of monoglycosylated alpha-D-pyranosylceramides plays a more important role in their immunostimulatory effects than the free 6"-hydroxyl group.
Uchimura
A
A
Pharmaceutical Research Laboratory, Kirin Brewery Co., Ltd., Gunma, Japan.
Shimizu
T
T
Morita
M
M
Ueno
H
H
Motoki
K
K
Fukushima
H
H
Natori
T
T
Koezuka
Y
Y
D000276:Adjuvants, Immunologic / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000818:Animals; D005260:Female; D005699:Galactosylceramides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005963:Glucosylceramides / Q000138:chemical synthesis* / Q000494:pharmacology*; D051379:Mice; D008807:Mice, Inbred BALB C; D008810:Mice, Inbred C57BL
C107484:AGL 517; D000276:Adjuvants, Immunologic; D005699:Galactosylceramides; D005963:Glucosylceramides; C103873:KRN 7000